WO1992018457A1 - Procede de tannage de peaux et composes utilisables a cet effet - Google Patents

Procede de tannage de peaux et composes utilisables a cet effet Download PDF

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Publication number
WO1992018457A1
WO1992018457A1 PCT/AU1992/000154 AU9200154W WO9218457A1 WO 1992018457 A1 WO1992018457 A1 WO 1992018457A1 AU 9200154 W AU9200154 W AU 9200154W WO 9218457 A1 WO9218457 A1 WO 9218457A1
Authority
WO
WIPO (PCT)
Prior art keywords
trimellitate
polyol
glycerol
ethylene glycol
pentaerythritol
Prior art date
Application number
PCT/AU1992/000154
Other languages
English (en)
Inventor
Peter Pojer
Kenneth Charles Montgomery
Chi Phuong Hunyh
Brian Milligan
Original Assignee
Commonwealth Scientific And Industrial Research Organisation
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Commonwealth Scientific And Industrial Research Organisation filed Critical Commonwealth Scientific And Industrial Research Organisation
Priority to US08/129,181 priority Critical patent/US5501708A/en
Priority to JP4507593A priority patent/JPH06506456A/ja
Priority to AU15522/92A priority patent/AU652442B2/en
Publication of WO1992018457A1 publication Critical patent/WO1992018457A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07H—SUGARS; DERIVATIVES THEREOF; NUCLEOSIDES; NUCLEOTIDES; NUCLEIC ACIDS
    • C07H13/00—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids
    • C07H13/02—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids
    • C07H13/08—Compounds containing saccharide radicals esterified by carbonic acid or derivatives thereof, or by organic acids, e.g. phosphonic acids by carboxylic acids having the esterifying carboxyl radicals directly attached to carbocyclic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/08—Preparation of carboxylic acid esters by reacting carboxylic acids or symmetrical anhydrides with the hydroxy or O-metal group of organic compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/76—Esters of carboxylic acids having a carboxyl group bound to a carbon atom of a six-membered aromatic ring
    • C07C69/80—Phthalic acid esters
    • C—CHEMISTRY; METALLURGY
    • C14—SKINS; HIDES; PELTS; LEATHER
    • C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
    • C14C3/00—Tanning; Compositions for tanning
    • C14C3/02—Chemical tanning
    • C14C3/04—Mineral tanning

Definitions

  • the present invention relates to a process for the preparation of tanned leather which utilises metals other than chromium, and to compounds for use in such a process.
  • leather is a material which is sensitive to heat when in a wetted state and may be subject to marked shrinkage which may occur abruptly over a relatively narrow temperature range.
  • the temperature which marks the onset of such shrinkage is known as the shrinkage temperature.
  • the shrinkage temperature differs according to the type of tanning material used and is thus used to characterise a particular type of leather.
  • chrome tanning agents generate pollution problems due to the effluent generated.
  • Concerns as to the carcinogenic nature of chromium (VI) compounds have lead to the introduction of chrome content restrictions for industrial effluent.
  • Aluminium tanning systems have been tried, however such systems suffer from three disadvantages. Firstly, aluminium binds to collagen over a very narrow pH range which is close to the precipitation point of the tanning salt. Secondly, the maximum shrinkage temperature obtainable with aluminium alone in the prior art has been approximately 80°C. This may be compared with chrome tanned leathers having shrinkage temperatures of between approximately 100°C and 125°C. Thirdly, aluminium tanned products deteriorate due to the fact that the aluminium may migrate out of the leather and is thus generally unstable over time. During wool skin dyeing for example, aluminium removal is a particular problem.
  • a process for the preparation of tanned leather which process includes
  • a metallic salt wherein the metal is -selected from chromium, aluminium, titanium or zirconium;
  • the leathers produced according to the process of the present invention may be characterised by improved hydrothermal stability as measured by an increase in shrinkage temperature.
  • the leather produced according to the process of the present invention may further be characterised by an excellent light fastness of the leather.
  • the skin or hide to be treated may be of any suitable type.
  • the skin or hide may be obtained from an ovine, porcine, bovine or caprine animal.
  • An ovine skin such as a wool skin is preferred.
  • the skin or hide may be pre-treated in any manner known per se, to prepare the hide for the tanning process.
  • a green hide may be used.
  • the hide may be pickled hide.
  • a pickled woolskin is preferred.
  • the process of the present invention may also be applied to a delimed hide, for example a delimed sheepskin pelt. It is accordingly unnecessary to submit the hide to a pickling and salt treatment step. This may reduce effluent and corrosion problems.
  • the metallic salt utilised to treat the skin or hide may be a chromium, aluminium, titanium or zirconium salt.
  • a chromium, aluminium, titanium or zirconium salt is used.
  • An aluminium salt is preferred.
  • Basic aluminium basic chloride, aluminium sulphate, aluminium formate or aluminium acetate may be used. Aluminium sulphate is preferred.
  • the metallic salt may be utilised in any suitable effective amount.
  • the metallic ion may be present in amounts of from approximately 0.25% to 10% by weight based on the moist weight of green hide.
  • the metal, e.g. aluminium ion is present in amounts of approximately 0.5% to 8% by weight.
  • the metallic, e.g. aluminium salt may be introduced in the form of a solution. An organic or aqueous solution may be used. An aqueous solution is preferred.
  • the hide may be contacted wfth the metallic salt for a period sufficient to permit binding of the metallic ions to the hide. Contact may continue for approximately 1 to 5 hours, preferably 2 to 4 hours.
  • the at least one organic polyolester of a polycarboxylic or hydroxycarboxylic acid may be of any suitable type.
  • a polyol ester of gallic acid, phthalic acid, 3,3',4,4' benzophenone tetracarboxylic acid, pyromellitic acid or trimellitic acid may be used.
  • a polyolester of trimellitic acid is preferred.
  • the polyolesters of trimellitic acid may exhibit superior light fastness relative to equivalent gallic acid esters.
  • a sugar or polysaccharide ester is preferred.
  • the polyol esters may be derived from ethylene glycol, propylene glycol, glycerol, mannitol, sorbitol, glucose, sucrose, lactose or pentaerythritol. Particularly preferred polyol esters may be selected from one or more of the ortho(o-), meta(m-) and para(p-) forms of
  • the polyolesters may be present in any isomeric form.
  • the at least one organic polyol ester of polycarboxylic acid or hydroxycarboxylic acid may be present in any suitable amounts.
  • the organic polyol esters may be present in amounts of from approximately 1% by weight to 20% by weight, preferably 5% to 15% by weight, based on the moist weight of green hide to be treated.
  • the organic polyolester may be provided in solution.
  • An aqueous or organic solution may be used.
  • An aqueous solution is preferred.
  • An aqueous solutio buffered to a pH of approximately 2.5 to 5 is preferred.
  • the organic polyol esters Whilst the mechanism of reaction is not known, it is postulated that the organic polyol esters increase the number of potential binding sites for the metallic ions. Accordingly, the organic polyol esters may be contacted with the hide or skin for a period sufficient for reaction to take place therebetween. A period of approximately 1 to 24 hours, preferably 5 to 10 hours, has been found to be suitable.
  • the contact steps may be conducted sequentially. However where the organic polyol esters are esters of gallic acid, the contact steps with organic polyolester may be conducted simultaneously with the contacting step utilising the metallic salts.
  • R6 is -(COOR 1 ) x , or
  • R 6 is H; or R 6 and R 7 together form ;
  • R 1 and R 2 are hydrogen or -OR 1 and -OR 2 together form an anhydride (- O -) bond; x is an integer of 0 or 1; and D is a polyol residue.
  • the polyol residue may be a sugar or polysaccharide moiety or
  • R 3 , R 4 and R 5 which may be same or different, are selected from hydrogen, hydroxyl, alkyl having 1 to 20 carbon atoms, hydroxy alkyl having 1 to 20 carbon atoms, or a compound of the formula
  • R 1 and R 2 are as described above, or mixtures thereof.
  • x is 1. More preferably y is an integer of 1 to 6.
  • organic polyol esters of this aspect of the present invention include ortho(o-), meta(m-) and para(p-) isomeric forms of the organic polyolesters of the present invention.
  • the organic polyol esters may be selected from o-, m- and p- forms of
  • lactose octagallate It has been found that the o-, m- and p- isomeric forms of the organic polyolesters may also function in the process of the present invention to significantly increase the shrinkage temperature of the tanned leather.
  • the shrinkage temperature may be increased to 100°C or greater to provide a boil proof leather.
  • a polyol selected from a polysaccharide, a sugar or a compound having the formula
  • Re are selected from hydrogen, hydroxyl, alkyl having 1 to 20 carbon atoms, hydroxy alkyl having 1 to 20 carbon atoms, or a compound of the formula
  • R 1 and R 2 are as described above; converting the polycarboxylic acid anhydride to an acid chloride;
  • the trimellitic acid anhydride may be converted to the acid chloride in known manner.
  • Thionyl chloride, phosphorous oxychloride, phosphorous pentachloride or the like may be used.
  • the polyol may be selected from ethylene glycol, glycerol, pentaerythritol, sorbitol, mannitol, sucrose, lactose and glucose.
  • the reaction between the trimellitic anhydride acid chloride and the polyalcohol may be conducted under basic, conditions. The reaction may continue for approximately 30 minutes to 4 days, depending on heat of reaction chosen.
  • the acid anhydride polyolester so formed may be converted to the dicarboxylic acid in known manner.
  • the compound may be left open to the atmosphere for an extended period. The compound thus takes up water from the atmosphere.
  • the compound may be treated with water, optionally in the presence of a small amount of acid or alkali.
  • R 1 , R 2 , R 6 , R 7 , D and x are as describe above, which process includes
  • R 7 is H; or R 6 and R 7 together form ;
  • x is 0 or 1
  • a polyol selected from & polysaccharide, a sugar or a compound having the formula
  • R 3 , R 4 and R 5 are selected from hydrogen, hydroxyl, alkyl having 1 to 20 carbon atoms, hydroxy alkyl having 1 to 20 carbon atoms, or a compound of the formula
  • R 1 and R 2 are as described above; and contacting the polycarboxylic acid anhydride with the polyol at elevated temperature for a period sufficient to permit reaction therebetween.
  • the reaction mixture may be heated to a temperature in the range of approximately 50°C to 300°C, preferably 100°C to 200°C.
  • the polyol may be selected from ethylene glycol, glycerol, pentaerythritol, sorbitol, mannitol, lactose, sucrose and glucose.
  • the process may be conducted in the solid phase, preferably at temperatures of about 150°C to 200°C.
  • a tanning composition including
  • a metallic salt wherein the metal is selected from chromium, aluminium, titanium or zirconium;
  • the metallic salt may be present in amounts of from approximately 5 to 50% by weight, preferably 5 to 15% by weight, based on the total weight of the tanning composition.
  • a chromium, titanium, aluminium or zirconium salt may be used.
  • An aluminium salt is preferred.
  • the at least one organic polyolester of a hydroxycarboxylic or polycarboxylic acid may be present in amounts of from approximately 50% to 95% by weight, preferably 85% to 95% by weight, based on the total weight of the tanning composition.
  • the polyolesters may be selected from one or more of
  • the organic polyol esters may be utilised in any suitable isomeric form.
  • the trimellitate esters are preferred.
  • the tanning composition may be provided in the form of a solution.
  • An organic or aqueous solution may be used.
  • the tanned leathers formed according to the process of the present invention may be subjected to further compounding steps as required.
  • the tanned leather so formed may be subjected to a dyeing process.
  • the tanned leather according to the present invention exhibits moderate to good dye bath stability.
  • leathers tanned with trimellitate esters may exhibit good dye bath stability.
  • compositions which may be utilised in the process of the present invention include agents which may improve the light fastness of the tanned leathers. Addition of such light fastness agents is preferred where the organic polyesters are organic polyesters of gallic acid.
  • the light fastness agents may include anti-oxidants, free radical scavengers and UV absorbers.
  • Trimellitic acid anhydride (3g) is dissolved in dimethyl formamide (DMF).
  • a polyol, pentaerythritol (0.5g) is added and the mixture heated at approximately 200oC for 2 hours.
  • Sifaltan-P (0.5 g) was dissolved in aqueous alkali buffer and pH was adjusted to approximately 3.5.
  • the pelt was drummed with a solution of aluminium sulphate (135g) in water (11) for 4 hours. It was then slowly basified to approximately pH 4.05 with 20% aqueous sodium carbonate solution (210ml), drummed 4 hours and allowed to stand overnight. It was then drained and washed with water, shrinkage temperature 91°C. Results are set out in Table 1 below.
  • the pickled wool-on skin (450g) was drummed overnight with an aqueous solution (900ml) of SIRALTAN-S (22.5 g, pH 4.6). It was then acidified with 1:1 formic acid as before, drained and washed.
  • SIRALTAN-PH is a sucrose octaphthalate carboxylate form of ethylene glycol diphthalate.
  • SIRALTAN-P, SIRALTAN-B and SIRALTAN-S are m-, p- carboxylate forms of pentaerythritol penta(trimellitate), sorbitol hexa(trimellitate) and sucrose octa(tri ⁇ nellitate) respectively.
  • Table 1 The results achieved in Table 1 may be contrasted with comparative results for chromium tannage in Table 2.
  • Tannage via the gallates can be performed in a concurrent process rather than a sequential one as described above.
  • the intestine pieces and mannitol hexagallate ester were mixed together in water and the aluminium solution was added at pH 2.5 (the pH of the aluminium solution). The pH was gradually raised to 3.4 with base at which point the intestines were left overnight. They were then washed. Ts ⁇ 100°.
  • Dye-bath conditions were: pH 3.1 aqueous formic acid, temperature 60°C. Tanned leather samples were shaken under these conditions and portions were removed regularly for shrinkage temperature determinations. pH was adjusted to 3.1, if necessary, with dilute formic acid.
  • the retanned sheepskin or intestine pieces from pretreatment or control processes were treated in aqueous solution of formic acid at pH 3.2-3.3 at 60°C for 6 hours. Samples were removed for shrinkage temperature measurements.
  • Sheep intestine with a pretan offer of 60% on dry weight Sheep intestine with a pretan offer of 60% on dry weight.
  • shrinkage temperatures were typically 76-79°C.
  • Retannage of the pretanned product with basified chromium sulphate gave leather with a Ts of 124°C compared with 105°C for skin tanned with the basified chromium sulphate alone.
  • Sheepskin pelts (1 + 1/2, drained pickled weight 600 g) were depickled in sodium chloride and sodium acetate to pH 4.8 and rinsed.
  • the 1-1/2 pelts were then pretanned with the BTDA/pentaerythritol (4:1) product to a final pH of 2. following overnight treatment.
  • the skins were washed and they were white with the feel and appearance of leather.
  • the 1-1/2 pretanned pelts plus control pickled 1/2 skin were then tanned with phthalate masked aluminiu sulphate plus sodium chloride to a final pH of 3.97.
  • Ts after retannage of pretanned 1/2 skin 99°C
  • Ts after aluminium tannage of control 1/2 skin 74°C (ie no pretannage).

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Health & Medical Sciences (AREA)
  • Biochemistry (AREA)
  • Biotechnology (AREA)
  • General Health & Medical Sciences (AREA)
  • Genetics & Genomics (AREA)
  • Molecular Biology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Treatment And Processing Of Natural Fur Or Leather (AREA)

Abstract

On décrit un ester de polyol organique d'un acide polycarboxylique ayant la formule (Para) et/ou (Méta) et/ou (Ortho) où R6 est -(COOR1)x, ou (I), R7 est H; ou R6 et R7 ensemble forment (II); R1 et R2 sont hydrogène ou -OR1 et -OR2 forment ensemble une liaison anhydride (-O-); x est un nombre entier valant 0 ou 1; Z est un nombre entier compris entre 1 et le nombre de groupes hydroxy du polyol et D est un groupe polyol. On décrit également des procédés de préparation desdits esters de polyol, une composition de tannage renfermant un sel métallique et un ester de polyol, ainsi qu'un procédé de tannage faisant emploi de ladite composition.
PCT/AU1992/000154 1991-04-09 1992-04-09 Procede de tannage de peaux et composes utilisables a cet effet WO1992018457A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
US08/129,181 US5501708A (en) 1991-04-09 1992-04-09 Process for tanning hides and compounds for use therein
JP4507593A JPH06506456A (ja) 1991-04-09 1992-04-09 獣皮のなめし方法とそれに用いるための化合物
AU15522/92A AU652442B2 (en) 1991-04-09 1992-04-09 Process for tanning hides and compounds for use therein

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
AUPK551091 1991-04-09
AUPK5510 1991-04-09
AUPL0950 1992-02-18
AUPL095092 1992-02-18

Publications (1)

Publication Number Publication Date
WO1992018457A1 true WO1992018457A1 (fr) 1992-10-29

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Country Status (5)

Country Link
US (1) US5501708A (fr)
EP (1) EP0580676A4 (fr)
JP (1) JPH06506456A (fr)
NZ (1) NZ242288A (fr)
WO (1) WO1992018457A1 (fr)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011085454A1 (fr) * 2010-01-18 2011-07-21 Katholieke Universiteit Leuven K.U.Leuven R&D Composés de benzènes et de saccharides se liant à gp120
WO2020104687A1 (fr) 2018-11-24 2020-05-28 Momentive Performance Materials Gmbh Utilisation de composés polyhydroxyaromatiques pour le traitement de substrats fibreux à base d'acides aminés
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US8679195B2 (en) * 2009-05-14 2014-03-25 Clariant Finance (Bvi) Limited Tanning process and tanning composition
EP2428503B1 (fr) * 2010-09-10 2014-12-10 Justus-Liebig-Universität Gießen Synthèse de dérivés de catéchol tripodaux flexibles pour la fonctionnalisation de surfaces
WO2012055480A1 (fr) * 2010-10-28 2012-05-03 Clariant International Ltd Tannage sans métaux
KR101849517B1 (ko) * 2010-10-28 2018-04-17 스탈 인터내셔날 비.브이. 비금속 태닝
US8801804B2 (en) * 2010-10-28 2014-08-12 Stahl International B.V. Non-metal tanning process
AU2011323042B2 (en) * 2010-10-28 2016-05-05 Stahl International Bv Non-metal tanning process
ES2618602T3 (es) * 2010-11-11 2017-06-21 Stahl International B.V. Curtido no metálico
EP2638180B1 (fr) * 2010-11-11 2014-11-26 Stahl International B.V. Tannage sans composés métalliques à l'activité tannage
AU2011328556B2 (en) * 2010-11-12 2016-10-06 Stahl International Bv Non metal tanning

Citations (8)

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US3183248A (en) * 1961-08-02 1965-05-11 Standard Oil Co Esters of trimellitic anhydride
GB1002190A (en) * 1963-06-06 1965-08-25 Boake Roberts & Co Ltd Esters of ester acids, their production and use
US3459733A (en) * 1964-10-15 1969-08-05 Mobil Oil Corp Monomeric polyesters of polyhydroxy compounds and process for preparing same
GB1222575A (en) * 1967-05-15 1971-02-17 Gen Electric Improvements in methods for preparing esters and amides of trimellitic anhydride and products therefrom
US4101271A (en) * 1976-06-12 1978-07-18 Bayer Aktiengesellschaft Tanning skins using polycarboxylic acid partial esters
GB1588047A (en) * 1977-09-09 1981-04-15 Ciba Geigy Ag Acid esters of trimellitic acid and their use as hardeners for epoxide resins
US4379886A (en) * 1980-04-28 1983-04-12 E. I. Du Pont De Nemours And Company Liquid coating composition having a reactive catalyst
US4902816A (en) * 1988-03-28 1990-02-20 Arco Chemical Technology, Inc. Polyols from phthalic compounds

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US3183248A (en) * 1961-08-02 1965-05-11 Standard Oil Co Esters of trimellitic anhydride
GB1002190A (en) * 1963-06-06 1965-08-25 Boake Roberts & Co Ltd Esters of ester acids, their production and use
US3459733A (en) * 1964-10-15 1969-08-05 Mobil Oil Corp Monomeric polyesters of polyhydroxy compounds and process for preparing same
GB1222575A (en) * 1967-05-15 1971-02-17 Gen Electric Improvements in methods for preparing esters and amides of trimellitic anhydride and products therefrom
US4101271A (en) * 1976-06-12 1978-07-18 Bayer Aktiengesellschaft Tanning skins using polycarboxylic acid partial esters
GB1588047A (en) * 1977-09-09 1981-04-15 Ciba Geigy Ag Acid esters of trimellitic acid and their use as hardeners for epoxide resins
US4379886A (en) * 1980-04-28 1983-04-12 E. I. Du Pont De Nemours And Company Liquid coating composition having a reactive catalyst
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Title
DERWENT ABSTRACT Accession No. 83-720334/30, Class B03; & JP,A,58 103 383 (NIPPON SHINYAKU KK), 20 June 1983 (20.06.83), see formula II. *
DERWENT ABSTRACT Accession No. 83-767128/38, Class B05; & JP,A,58 032 875 (NIPPON SHINYAKU KK), 25 February 1983 (25.02.83), see formula III. *
DERWENT ABSTRACT Accession No. 84-217121/35, Class B03; & JP,A,59 128 329 (TANAKA Y), 24 July 1984 (24.07.84), see formula I. *
DERWENT ABSTRACT Accession No. 86-186048/29, Class B03; & JP,A,61 118 395 (NIPPON SHINYAKU KK), 5 June 1986 (05.06.86), see formula II. *
DERWENT ABSTRACT Accession No. 88-165732/24, Class B03; & JP,A,63 104 927 (TSUMURA JUNTENDO KK), 10 May 1963 (10.05.63), see formula II. *
DERWENT ABSTRACT Accession No. 88-238133/34, Class B04; & JP,A,63 170 319 (SANTEN SEIYAKU KK), 14 July 1988 (14.07.88). *
PATENT ABSTRACTS OF JAPAN, C-109, page 10; & JP,A,57 038 749 (KURARAY KK), 3 March 1982 (03.03.82). *
PATENT ABSTRACTS OF JAPAN, C-109, page 10; & JP,A,57 038 750 (KURARAY KK), 3 March 1982 (03.03.82). *
PATENT ABSTRACTS OF JAPAN, C-194, page 147; & JP,A,58 140 046 (SHIYOUFUU TOUSHI SEIZOU KK), 19 August 1983 (19.08.83), see formulae I and II. *
PATENT ABSTRACTS OF JAPAN, C-194, page 147; & JP,A,58 140 047 (SHIYOUFUU TOUSHI SEIZOU KK), 19 August 1983 (19.08.83), see formula I. *
PATENT ABSTRACTS OF JAPAN, C-194, page 147; & JP,A,58 140 048 (SHIYOUFUU TOUSHI SEIZOU KK), 19 August 1983 (19.08.83), see formula I. *
See also references of EP0580676A4 *

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011085454A1 (fr) * 2010-01-18 2011-07-21 Katholieke Universiteit Leuven K.U.Leuven R&D Composés de benzènes et de saccharides se liant à gp120
US11179312B2 (en) 2017-06-05 2021-11-23 Momentive Performance Materials Inc. Aqueous compositions for the treatment of hair
WO2020104687A1 (fr) 2018-11-24 2020-05-28 Momentive Performance Materials Gmbh Utilisation de composés polyhydroxyaromatiques pour le traitement de substrats fibreux à base d'acides aminés
CN113329993A (zh) * 2018-11-24 2021-08-31 迈图高新材料有限责任公司 多羟基芳族化合物用于处理基于氨基酸的纤维状基质的用途
US11090255B2 (en) 2018-12-04 2021-08-17 Momentive Performance Materials Inc. Use of polycarboxylic acid compounds for the treatment of fibrious amino acid based substrates, especially hair

Also Published As

Publication number Publication date
EP0580676A1 (fr) 1994-02-02
JPH06506456A (ja) 1994-07-21
US5501708A (en) 1996-03-26
EP0580676A4 (fr) 1995-02-22
NZ242288A (en) 1994-10-26

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